Compound having carbazole ring structure, and organic electroluminescent device

Abstract

There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has high triplet exciton confining capability with an electron blocking ability, and that has high stability in the thin-film state and high luminous efficiency. The compound is used to provide a high-efficiency, high-durability organic electroluminescent device, particularly a phosphorescent organic electroluminescent device. The present invention is a compound of the following general formula having a carbazole ring structure. The compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.

1 . A compound of the following general formula (1) having a carbazole ring structure, 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  may be the same or different, and represent a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, r 1 , r 4 , and r 5  may be the same or different, and represent 0 or an integer of 1 to 4, r 2 , r 3 , and r 6  may be the same or different, and represent 0 or an integer of 1 to 3, n represents 1, Ar 1 , Ar 2 , and Ar 3  may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and wherein at least one of R 1  to R 6 , or at least one of the substituents of Ar 1  to Ar 3  is a deuterium atom, or a substituent that contains a deuterium atom. 
     
     
         2 . The compound having a carbazole ring structure according to  claim 1 , wherein Ar 2  in the general formula (1) is a monovalent group represented by the following general formula (2) or (3), 
       
         
           
           
               
               
           
         
       
       wherein R 7  and R 8  may be the same or different, and represent a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, r 7  represents 0 or an integer of 1 to 4, r 8  represents 0 or an integer of 1 to 3, B represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon group, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of a substituted or unsubstituted condensed polycyclic aromatic group, Ar 4  represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and wherein at least one of R 7  and R 8 , or at least one of the substituents of Ar 4  or B is a deuterium atom, or a substituent that contains a deuterium atom, 
       
         
           
           
               
               
           
         
       
       wherein R 9  and R 10  may be the same or different, and represent a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, r 9  and r 10  may be the same or different, and represent 0 or an integer of 1 to 3, C represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon group, a divalent group of a substituted or unsubstituted aromatic heterocyclic ring, or a divalent group of a substituted or unsubstituted condensed polycyclic aromatic group, Ar 5  represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, W, X, Y, and Z represent a carbon atom or a nitrogen atom, where only one of W, X, Y, and Z is a nitrogen atom, and, in this case, the nitrogen atom does not have the substituent R 9 , and wherein at least one of R 9  and R 10 , or at least one of the substituents of Ar 5  or C is a deuterium atom, or a substituent that contains a deuterium atom. 
     
     
         3 . (canceled) 
     
     
         4 . (canceled) 
     
     
         5 . The compound having a carbazole ring structure according to  claim 1 , wherein the compound is represented by the following general formula (1′), 
       
         
           
           
               
               
           
         
       
       wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6  may be the same or different, and represent a deuterium atom, a fluorine atom, a chlorine atom, cyano, trifluoromethyl, nitro, linear or branched alkyl of 1 to 6 carbon atoms that may have a substituent, cycloalkyl of 5 to 10 carbon atoms that may have a substituent, linear or branched alkyloxy of 1 to 6 carbon atoms that may have a substituent, cycloalkyloxy of 5 to 10 carbon atoms that may have a substituent, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or substituted or unsubstituted aryloxy, r 4  and r 5  may be the same or different, and represent 0 or an integer of 1 to 4, r 1 , r 2 , r 3 , and r 6  may be the same or different, and represent 0 or an integer of 1 to 3, Ar 1 , Ar 2 , and Ar 3  may be the same or different, and represent a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group, and wherein at least one of R 1  to R 6 , or at least one of the substituents of Ar 1  to Ar 3  is a deuterium atom, or a substituent that contains a deuterium atom. 
     
     
         6 . An organic electroluminescent device that comprises a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes,
 wherein the compound having a carbazole ring structure of  claim 1  is used as a constituent material of at least one organic layer.   
     
     
         7 . The organic electroluminescent device according to  claim 6 , wherein the organic layer is a hole transport layer. 
     
     
         8 . The organic electroluminescent device according to  claim 6 , wherein the organic layer is a hole injection layer. 
     
     
         9 . The organic electroluminescent device according to  claim 6 , wherein the organic layer is an electron blocking layer. 
     
     
         10 . The organic electroluminescent device according to  claim 6 , further comprising a light emitting layer that contains a phosphorescent light-emitting material. 
     
     
         11 . The organic electroluminescent device according to  claim 10 , wherein the phosphorescent light-emitting material is a metal complex that contains iridium or platinum. 
     
     
         12 . An organic electroluminescent device that comprises a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes,
 wherein the compound having a carbazole ring structure of  claim 2  is used as a constituent material of at least one organic layer.   
     
     
         13 . The organic electroluminescent device according to  claim 12 , wherein the organic layer is a hole transport layer. 
     
     
         14 . The organic electroluminescent device according to  claim 12 , wherein the organic layer is a hole injection layer. 
     
     
         15 . The organic electroluminescent device according to  claim 12 , wherein the organic layer is an electron blocking layer. 
     
     
         16 . The organic electroluminescent device according to  claim 12 , further comprising a light emitting layer that contains a phosphorescent light-emitting material. 
     
     
         17 . The organic electroluminescent device according to  claim 16 , wherein the phosphorescent light-emitting material is a metal complex that contains iridium or platinum.